The instant substituted 1,4-diamino-2-butyne and propargylamine compounds fall into three general groups depending on the various substituents on the N-atoms.
When said substituents are alkyl, cycloalkyl, substituted alkyl or aryl some such compounds are described in British Patent No. 595,540, but no utility for said compounds is disclosed other than as intermediates to make other compounds.
When said substituents are aryl, British Patent No. 1,438,482 generically describes lubricant compositions containing substituted aryl amines of the formula R--X where R is a secondary amine residue containing two aromatic groups attached to nitrogen such as (Ar).sub.2 N--. The group X is inter alia propargyl. This reference also generically describes compounds of the formula R--Y--R where Y is inter alia --CH.sub.2 CH.tbd.CHCH.sub.2 --. The only such compounds specifically disclosed by the British reference are those where R is an alkylated phenothiazine moiety. The closest compound of this reference is N-propargyl-3,7-dioctylphenothiazine).
British Patent No. 1,438,482 does not disclose or suggest that the compounds described therein can provide effective antioxidant protection to synthetic polymer compositions.
J. d'Angelo, J. Bull. Chim. Soc. France, 1970, 2415 describes the preparation of 1,4-bis(diphenylamino)-2-butyne in a theoretical study on isomerization. No utility for said compound is disclosed.
A. Mostamandi et al., Z. Org. Khim. 18, 977 (1982) describe the preparation of N,N-diphenylpropargylamine by the reaction of propargyl bromide and diphenylamine in the presence of acetonitrile and tetraethylammonium iodide catalyst and base. No utility is disclosed for said compound.
1,4-Bis(hexamethyleneimino)-2-butyne and N-propargylhexamethyleneimine are reported as corrosion inhibitors for steel by C. Guido Yanez et al., Azer. Inst. Neft. Khim, 25, 52, 88 (1982) [Chem. Abst. 97, 201547k (1982)].
European Patent Application 101,411 (Chem. Abst. 100, 211061s) teaches hindered amine polymer stabilizers containing 2,4-bis(propargylamino)-s-triazin-6-yl moieties.